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Regrets—The Big Five

Vivia Chen

January 16, 2013

© ampyang - Fotolia.comI 'm suspicious of people who say they wouldn't change a thing if they had the chance to do their lives over again. They strike me as a bit smug. Or shallow. Or just dishonest.

I'm the opposite extreme—and that's not healthy either. I tend to berate myself for the stupid things I've done in my life—and all the clever things I failed to do. There's not much point in replaying those mistakes—unless you can learn something from it.

Of course, that's the conceit of articles about life's regrets. The latest of that genre is from tech entrepreneur Daniel Gulati. In the Harvard Business Review Blog Gulati describes the top five career regrets:

1. "I wish I hadn't taken the job for the money." In his study, Gulati finds that the "biggest regret of all came from those who opted into high-paying but ultimately dissatisfying careers."

2. "I wish I had quit earlier." Most who eventually left their jobs to pursue their true passions expressed regret that they had not done so earlier, says Gulati.

3. "I wish I had the confidence to start my own business." Once they stashed away enough money, Gulati finds, most professionals "yearned for more control over their lives," meaning they wanted to "become an owner, not an employee in someone else's company."

4. "I wish I had used my time at school more productively." One example of this regret is hurrying through the college years, which, as one biology researcher recounted to Gulati, "were the best and most delightfully unstructured years of my life."

5. "I wish I had acted on my career hunches." Though Gulati calls them "hunches," I think he's actually talking about risks/challenges not taken. (He cites an investment banker who declined to lead a team into Latin America, thus missing a key opportunity for promotion.) The key, Gulati says, is to identify the "unpredictable but potentially rewarding moments of change, and jumping on these opportunities." 

I can't really quarrel with Gulati's list, except for a few points. First, I'm not sure it's so awful to take a job for the money. Why not sell yourself to the highest bidder and sock away the money so that you can eventually pursue the other things on that list? The trick, I guess, is not to be so sucked in by the big bucks that you can't leave when you're truly miserable.

As for starting your own business, I think the entrepreneurial thing has been oversold. It's not for everybody. Most lawyers I know—particularly those born and raised in big firms—would be helpless lambs on their own.

But my main quibble with Gulati is that he makes such a clean distinction between the professional and the personal. In fact, he pretty much omits the personal stuff altogether. Many people (or is it just women?) will tell you there's a big overlap between the two realms. Often, there's a lover or spouse who has influenced the trajectory of their careers. Sometimes that influence was wonderful and propelled their careers in unexpected ways. Oftentimes, it was an emotional drain, a career hindrance, and a big waste of time. The point is that the choices you make in your personal life can have a huge impact on your career.

Anything you'd like to add to that list of regrets? And do we really learn from our mistakes?

Do you have topics you'd like to discuss or tips to share? Email chief blogger Vivia Chen at [email protected] 

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Meh. The irony here is that I, as a midlevel associate in biglaw, am stuck in it because the pay is far too low to quit - it just takes too long to pay off law school and to have the cash needed to move on. Likewise, I suspect that almost all of my junior associates would quit - and potentially move to higher paying jobs - if they weren't saddled with mountains of law school debt.

So the irony is that, in biglaw, the issue I've seen is, in fact, that the job pays horribly relative to the debt, making it impossible to quit to retool and take a job that actually pays enough to allow you to actually do something you'd like to do.

In biglaw, when does this threshold occur? At 40? 45?

The "I'm sorry I did it for the money argument" just isn't an issue when you come out of school with $200k of debt and then work for years doing what amounts to unskilled secretarial work (which is also why the big law lambs would be slaughtered if working on their own - not because they started off any worse, but because they acquire no real world skills and literally often don't even know how basic law firm business operations work because they've been too busy making tables of precedent M&A deal terms).

To Rob, one suggestion. Tell her. Not to get her back, but to set the record straight--for both of you. You owe her (and yourself) that much.

I believe that regrets are an integral part of our individual “journey”, i.e., what results when we have not listened to our inner voice or knowingly put on blinders. I think regrets are unavoidable, however, they can certainly be minimized if we regularly reevaluate our decisions and circumstances. I think the key is to make every attempt to know what your personal definition of “success” is. Let it be your guide!

I know we all can come up with scenarios where, with our 20/20 hindsight, we coulda, shoulda, woulda. The grass is always greener on the other side of the fence. Make it a point to start with today and move in the direction you desire for your future.

I wish I had manned up when I was 25 years old during my 1L year when I accidentally got my 19 year old girlfriend pregnant her sophomore year of college.

She offered to move in with me and said she wanted to keep the baby and raise a family with me, but I declined. Then I pressured her to have an abortion against her wishes, and ended up breaking up with her afterwards. It was all very ugly, and I'm the one to blame.

It's taken nearly 10 years for me to come to grips with it, but I thought I couldn't handle a family and law school back then, so I ran from my obligation, under the pretense of "its really best for both of us"; when I'm not really sure it was. I still finished law school, and she finished college, even though she became a chainsmoking nervous wreck after the abortion, then went on to grad school, then moved to Boston and has been in a relationship with a good guy for the past several years. Although she still chainsmokes like a chimney, she seems to have moved on with her life, and I'm genuinely happy for her; even though she hasn't spoken to me in years. Meanwhile, I'm riddled with guilt, drinking problems, and an awkward start to my career that I suppose is deserved.

I really Regret the way I handled it, because it really did impact my career choices, with me choosing more conservative regional career options, dating less exceptional women, and generally struggeling to find happiness. When I think that if we had stayed together and kept the baby our daughter would turn 10 years old this year, it makes me want to cry. Instead, Im childless, divorced, fat, and balding, in my mid thirties. Again, I have no one to blame for that by myself, but its definitelty #1 on my Regrets.

I suggest all career women -- especially female lawyers facing a long haul to partnership -- consider whether they will regret delaying childbearing. I waited until after I made partner at Big Law. Here's my take on that issue. http://womensrightswriter.com/articles/if-i-could-do-it-again-would-i-still-wait-to-have-children/


The only regrets I believe in is missing live theatre - such as when I missed seeing Anthony Hopkins and Vanessa Redgrave in Antony and Cleopatra when I was a 19-year-old college kid in London in 1987 because I'd rather sleep in.

I agree. I followed my passion and worked in nonprofits for more than 25 years. Now I'm 20 years from retirement and wondering how I'm going to pay for it. I wish I had followed the money earlier and saved the world in my free time.

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About The Careerist

The Careerist takes an inside look at how lawyers shape their careers and manage their lives. The blog aims to dissect developments in the profession, provide useful information and advice, and give lawyers a platform to voice their views. The goal is to provide a fresh, provocative take on the state of lawyering.

About Vivia Chen

Vivia Chen

Vivia Chen, The Careerist's chief blogger, has been covering the business and culture of law firms for a decade. A former corporate lawyer, Chen is fascinated by those who thrive (as well as those who don't) in the legal profession. Her take: Success in the law (and life) doesn't always travel a linear path. If you have topics you'd like to discuss or information to share, contact her: [email protected]

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